Thionyl Chloride → 2-(3-Dimethylamino-butyl)-1-phenyl-1H-quinazolin-4-one

HRID 557123

Reaction equation

HRID 557123 reaction equation
[CH3:1][N:2]([CH:4]([CH2:8][CH2:9][CH3:10])[C:5](O)=O)[CH3:3].S(Cl)(Cl)=O.[C:15]1([NH:21][C:22]2[CH:30]=[CH:29][CH:28]=[CH:27][C:23]=2[C:24]([NH2:26])=[O:25])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClC(Cl)Cl>[CH3:1][N:2]([CH3:3])[CH:4]([CH3:5])[CH2:8][CH2:9][C:10]1[N:21]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:22]2[C:23]([C:24](=[O:25])[N:26]=1)=[CH:27][CH:28]=[CH:29][CH:30]=2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 964552-(Phenylamino)BenzamideHCID 178834622-(Dimethylamino)pentanoic acid

Product 1

HCID 669916512-(3-Dimethylamino-butyl)-1-phenyl-1H-quinazolin-4-one

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
57.5 °C

Procedure

3.80 g (20.9 mmol) dimethylamino-pentanoic acid were added to 25 ml thionyl chloride and stirred for 90 min. at 55-60° C. The remaining thionyl chloride was distilled in vacuum and the residue was added to a solution of 2.00 g (9.42 mmol) 2-phenylamino-benzamide (see above) in 30 ml trichloromethane at 0° C. The reaction mixture was boiled for 4 h and stirred overnight at room temperature. The residue was filtrated and dissolved in dichloromethane and saturated sodium bicarbonate solution. The organic solvent was dried over magnesium sulfate and evaporated. The yellow oil slowly crystallized.

Workup

  1. distillationThe remaining thionyl chloride was distilled in vacuum
  2. waitThe reaction mixture was boiled for 4 h
  3. stirringstirred overnight at room temperature
  4. filtrationThe residue was filtrated
  5. dissolutiondissolved in dichloromethane
  6. dry with materialThe organic solvent was dried over magnesium sulfate
  7. customevaporated
  8. customThe yellow oil slowly crystallized

Sources & evidence

ORD record
ord-2c9c8312544845c88e1ce53cde67ccbd
Source dataset
uspto-grants-2011_11
Patent number
US08058431B2

Linked notes

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